September has a funny way of feeling like the end of something.

Summer trips are over. School is back. Calendars refill. And travel gets pushed into that vague category of maybe after the holidays.

I’d argue this is exactly when you should be traveling.

Because I went shopping—and some of the most interesting luxury travel opportunities of the year are still sitting right in front of us. Not trips to bookmark for next fall.

Trips you can actually take now!

Here are seven you should be looking at right now.

Passalacqua | Lake Como, Italy

1 | LAKE COMO, ITALY

WHY | You can experience Passalacqua after everyone thinks Como is over.

WHEN | November 15-17

Lake Como may be synonymous with summer, but one of its greatest hotels makes a compelling argument for visiting later in the year.

Unlike many of the lake’s seasonal hotels, Passalacqua stays open through the holidays, closing only from early January until early March. And November isn’t simply summer Como minus the boats. The experience changes with the season: chestnut walks, new-pressed olive oil, white truffles, cooking classes, afternoons by the fire and Thursday dinners in the wine cellar. Passalacqua even notes that lunches beside the lake can linger outdoors well into December.

And then there is the price.

WHAT I FOUND | November 15–17 is currently showing entry rooms from approximately $1,150 per night—roughly 70% below the tracked peak-season benchmark of $4,156 per night.

That is not settling for Lake Como in November.

That is getting Passalacqua in November.

FTN TAKE | Stay three or four nights and resist every temptation to over-schedule it. At this time of year, the hotel isn’t merely where you sleep. It’s the reason you came.

See what autumn looks like at Passalacqua, then come back to us when you’re ready to make it yours—we’ll handle the stay with our preferred partner amenities, upgrade opportunities and VIP touches.

Gleneagles | Perthshire, Scotland

2 | GLENEAGLES, SCOTLAND

WHY | Peak Gleneagles—without the peak-season price.

WHEN | Any midweek now through October

There are hotels that work in autumn. And then there is Gleneagles.

The 850-acre Scottish estate was practically made for this moment: falconry, countryside walks, shooting, golf, spa afternoons, long dinners and the rather appealing prospect of returning from all of it to a roaring fire.

But here’s the reason I’d look now.

WHAT I FOUND | Book two nights or more midweek through October 2026 and Gleneagles is currently offering up to 20% off its best available rate. Breakfast at The Strathearn and use of the swim and gym facilities are included.

The hotel is also currently advertising its Strathearn Soirée from £725, including bed, breakfast and a three-course dinner, while its Tee It Up package starts from £955, including one night and a round on one of its three championship golf courses.

Suddenly, going later isn’t just atmospheric. Nothing about the experience feels off-season—except, perhaps, the price.

FTN TAKE | I’d give Gleneagles three nights rather than two and pair it with Edinburgh. This is the grand Scottish country-house fantasy at precisely the moment the country-house part gets really good.

See what’s happening at Gleneagles this October, then come back to us to arrange your stay with our preferred partner amenities, upgrade opportunities and VIP recognition.

Four Seasons George V | Paris, France

3 | PARIS, FRANCE

WHY | Paris is always a good idea. Especially when the Saints are playing.

WHEN | October 23-26

This one requires considerably less convincing around here.

On Sunday, October 25 at 2:30 PM, the New Orleans Saints face the Pittsburgh Steelers at Stade de France in the first regular-season NFL game ever played in France.

And as of now, you haven’t necessarily missed it.

WHAT I FOUND | October 23–26 isn’t sold out—not even close. But the Saints are definitely moving the needle.

There is still a surprisingly good range of luxury inventory showing in Paris, from intimate Left Bank stays to the grand palaces. Relais Christine is currently showing rooms from approximately $1031 per night, while Saint James Paris starts around $1522 per night. At the palace end of the spectrum, Four Seasons Hotel George V, Le Bristol Paris and Mandarin Oriental Lutetia are running roughly $3,000-4,000 per night in late October, depending on the night, room category.

And, of course, Filling the Nest clients can see even more value at these stays through our preferred partnerships—with benefits such as upgrades confirmed at booking, complimentary private transfers, daily breakfast, food-and-beverage credits and other VIP amenities, depending on the property and program.

And you can still get into the game. Official Saints–Steelers tickets for Sunday, October 25 are currently on sale starting at $160pp,

Football may be the reason you go, but it certainly doesn’t have to be the reason you linger.

Come for the Saints, then give Paris the time it deserves—Champagne, shopping, long lunches, fabulous dinners, and a few days to remember why Paris is always a good idea.

Need more inspiration? We’ve already made the case for turning game weekend into something much bigger in Saints & Savoir Faire.

FTN TAKE | Three nights. One football game. The rest is Paris. And unlike “Paris in October,” the first Saints game in Paris only happens once.

Ticket prices converted to USD using the September 1, 2026 exchange rate and are approximate.

Four Seasons Yachts | Mediterranean

4 | THE MEDITERRANEAN

WHY | There’s still room aboard Four Seasons I.

WHEN | October – November

Here’s the one that might surprise you.

The highly anticipated Four Seasons I began sailing earlier this year, and despite the eager anticipation, several of its inaugural-season Mediterranean voyages are still showing availability.

Not waitlist. Not “inquire for 2027.”

Reserve Now.

WHAT I FOUND | And these prices are per suite, not per person!

October 4–9 | 5 nights
The Rivieras featuring Portovenere & Cannes
From $24,869 per suite

October 9–18 | 9 nights
The Rivieras featuring Argentario & L’Île-Rousse
From $32,888 per suite

October 18–25 | 7 nights
The Rivieras featuring Portoferraio & Saint-Tropez
From $27,800 per suite

October 25–November 1 | 7 nights
The Rivieras featuring Nice & Valencia
From $26,700 per suite

November 1–8 | 7 nights
Grand Mediterranean featuring Casablanca & Lanzarote
From $25,600 per suite

And if you’re on the fence about whether or not cruising is for you, how about the perfect teaser voyage:

November 16-19 | 3 nights
Lesser Antilles featuring St. Barth’s and Antigua
From $12,200 per suite

Know one thing – This is not a conventional cruise ship with a prettier logo attached. Four Seasons I carries just 95 suites, all with private terraces, with the space, service and residential feeling designed to feel much closer to a private yacht.

FTN TAKE | If you’ve spent years telling me, I’m not a cruise person, this is precisely the one I’d put in front of you.

Nemacolin | Farmington, Pennsylvania

5 | NEMACOLIN, PENNSYLVANIA

WHY | Fall foliage, but make it spooky.

WHEN | October 30-November 1

I recently told Forbes that September may be one of luxury travel’s best-kept secrets, and Nemacolin is exactly the sort of place I had in mind.

Set across 2,200 acres in Pennsylvania’s Laurel Highlands, this isn’t a leaf-peeping road trip requiring a cooler and sensible shoes. You get the fall landscape—and then return to serious dining, spa, golf, art, outdoor adventures and several very different versions of luxury accommodation.

But I’d circle one weekend in particular.

WHAT I FOUND | October 30–November 1: Nemacolin’s Mountain Masquerade Halloween package is currently bookable with a two-night minimum including Saturday, October 31.

The package includes your room, the Pumpkin Patch Lounge reception, admission to the Mountain Masquerade and a $35-per-person breakfast allowance plus a $125-per-person dinner allowance.

Booked separately, the October 31 Mountain Masquerade party itself is $125 per person, plus tax and gratuity, and includes a live DJ and a costume contest with a $10,000 cash prize.

Not quite your standard Pennsylvania foliage weekend.

If Halloween isn’t your thing, Nemacolin’s current Experience Package offers $200 in resort credit for two nights, $300 for three, $400 for four or $500 for five, subject to applicable dates and restrictions.

FTN TAKE | This is one of the easiest trips on this list to pull together quickly. Three nights, very little logistical gymnastics, and plenty to do once you arrive.

Rocky Mountaineer | Canada

6 | THE CANADIAN ROCKIES

WHY | You should catch the last train before winter.

WHEN | Early October

There is something particularly appealing about a trip with an actual season finale.

Rocky Mountaineer winds down its Canadian Rockies rail season in October. Once those final trains roll, this isn’t a trip you postpone for a few weeks.

You wait until next year.

The classic First Passage to the West travels between Vancouver and Banff/Lake Louise, crossing the Continental Divide and the Canadian Rockies during daylight hours with an overnight in Kamloops.

WHAT I FOUND | Select October 2026 First Passage to the West departures are still being offered, including late-season dates into approximately October 11–12. Rail-only GoldLeaf itineraries have been advertised from approximately $2,890 per person, while longer GoldLeaf Canadian Rockies packages with early-October departures are currently being offered from approximately $7,133 per person.

This is the one where I’d move quickly rather than shop endlessly. Late-season availability is selective, not broad, and some 2026 itineraries are already sold out.

And yes, I’d choose (and have experienced) GoldLeaf: bi-level glass-dome coaches upstairs, dining below and the Canadian Rockies providing the entertainment. It’s really the only way to go.

FTN TAKE | Don’t fly all that way for two days on a train. Put Vancouver on one end and Banff or Lake Louise on the other and make it a proper week.

The Colony Hotel | Palm Beach, Florida

7 | PALM BEACH, FLORIDA

WHY | Pink looks even better before peak-season pricing.

WHEN | November before Thanksgiving

Palm Beach’s beloved Pink Paradise doesn’t need a January social calendar to be fabulous.

Come in late September or early October for Swifty’s by the pool, Worth Avenue around the corner, and beach days delivered Colony-style—before the winter crowds arrive and peak-season rates take over.

WHAT I FOUND | September pricing is when things at The Colony get interesting. I found rates starting around $402 per night, and the hotel is also offering up to 20% savings on stays of three nights or longer through September 30, making a late-September long weekend particularly compelling.

FTN TAKE | This may be one of my favorite examples of the Luxury of Going Later. Nothing about The Colony feels “off-season”—the hotel is still fabulously pink, Swifty’s is still buzzing around the pool, Worth Avenue is still steps away, and Palm Beach is still Palm Beach. You’re simply getting there before everyone else flies south. Three nights in late September, please. Pink looks even better at $400-something a night.

The point isn’t just where. It’s when.

There will always be another summer in Europe. Another peak season. Another reason to wait until the calendar tells us it’s officially time to travel again.

But some opportunities don’t work that way.

A yacht has a sailing date. A train runs its final route of the season. A football game happens once. A promotion expires. A legendary hotel has a room available at a price that makes you look twice.

And sometimes the place you’ve always imagined seeing at its busiest turns out to be even better after everyone else has gone home.

So if one of these made you stop for a second, pay attention.

Fall isn’t what’s left of the travel year.

It might just be the best kept luxury travel secret of all.

THE EDIT | READ NEXT

The Luxury of Going Later

Peak luxury and peak season aren’t necessarily the same thing. Here’s why some of our favorite places get even better once everyone else goes home.

READ THE FEATURE →

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Rates, promotions and availability checked September 1, 2026 and subject to change. All rates are starting rates unless otherwise noted and may exclude taxes, fees and other charges.